JP2002187873A - Method for purifying optically active 1-(trifluromethyl monosubstituted phenyl)ethylamine - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method with which an optically active 1-(trifluoromethyl monosubstituted phenyl)ethylamine being an important intermediate for a medicine and an agrochemical can be purified industrially simply and efficiently in a high optical purity. SOLUTION: An optically active 1-(trifluoromethyl monosubstituted phenyl) ethylamine is made into an inorganic acid or organic acid salt, purified by recrystallization so that the compound is purified in a high optical purity.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a purification method for obtaining optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine, which is an important intermediate of pharmaceuticals and agricultural chemicals, with high optical purity.

[0002]

BACKGROUND OF THE INVENTION Optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamines are important intermediates in pharmaceuticals and pesticides. Regarding the method for producing the optically active amine, for example, in the case of an ortho-trifluoromethyl form (2-trifluoromethyl form), J. Am. Chem. Soc., 112,
5741-5747 (1990); J. Chem. Soc., P.
The synthesis is performed with reference to the asymmetric reduction of an oxime derivative described in erkin Trans. 1, 2039 (1985). Its chemical yield and optical purity are 16% and 76% ee (S), respectively.

[0003] The meta-trifluoromethyl form (3-trifluoromethyl form) is reported in JP-A-9-278718, in which optical resolution is carried out with L-mandelic acid. The chemical yield and optical purity from the crystals of the precipitated diastereomer salt were 45% and 60% ee, respectively.
(S), and the chemical yield and optical purity of the mother liquor and the crystal from the washing solution are 55% and 50% ee (R), respectively. It can also be synthesized by the method described in the ortho-trifluoromethyl form, and its chemical yield and optical purity are 19% and 87% ee (S), respectively (J. A.
m. Chem. Soc., 112, 5741-5747 (1990)).

In the case of para-trifluoromethyl form (4-trifluoromethyl form), J. Am. Chem. Soc., 105, 1
578-1584 (1983). In optical resolution with LN-acetylleucine, the crystals of the precipitated diastereomeric salt are recrystallized three times. Its chemical yield and optical purity are 19% and 60% ee (S), respectively. It can also be synthesized by a non-enzymatic enantioselective acylation reaction using a planar-chiral derivative of 4-pyrrolidinopyridine, and by using (−)-Ph-PPY *, unreacted Is reported to be enriched. However, its chemical yield and optical purity are not described (Chem. Commun., 2000, 119-120).

In the above-mentioned synthesis method, the optically active amine cannot be obtained with high optical purity and high yield, and it is not a simple and efficient production method from an industrial viewpoint.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a method for preparing a synthetic intermediate of an optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine by converting it into a salt of an inorganic acid or an organic acid and purifying it by recrystallization. The objective is to obtain 1- (trifluoromethylmonosubstituted phenyl) ethylamine of optical purity.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, have found that optical activity 1-
By synthesizing the intermediate of (trifluoromethylmonosubstituted phenyl) ethylamine as a salt of an inorganic acid or an organic acid and recrystallizing the same, 1- (trifluoromethylmonosubstituted phenyl) ethylamine having high optical purity can be obtained. Revealed.

That is, the present invention provides a compound represented by the general formula [1]:

[0009]

Embedded image

[Wherein, R represents an optically active α-arylethyl group represented by C * HMeAr, Ar represents a phenyl group or 1 or 2-naphthyl group, and * represents an asymmetric carbon] Wherein the optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine represented by the formula (1) is converted into a salt of an inorganic acid or an organic acid and purified by recrystallization.

Further, the present invention provides a compound represented by the general formula [1]:

[0012]

Embedded image

[Wherein, R represents an optically active α-arylethyl group represented by C * HMeAr, Ar represents a phenyl group or 1 or 2-naphthyl group, and * represents an asymmetric carbon] And salts of inorganic or organic acids of optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamines represented by

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION The method for purifying optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine of the present invention will be described in detail below.

The optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamines represented by the general formula [1] of the present invention include those represented by the formula [2]

[0016]

Embedded image

Trifluoromethylmono-substituted phenylmethyl ketone represented by the general formula [3]

[0018]

Embedded image

[In the formula, Ar represents a phenyl group or 1 or 2-naphthyl group, and * represents an asymmetric carbon.] The optically active primary amine represented by the following formula is obtained by dehydration condensation under acidic conditions. General formula [4]

[0020]

Embedded image

Wherein Ar represents a phenyl group or a 1- or 2-naphthyl group, and * represents an asymmetric carbon. The compound can be produced by asymmetric reduction of an optically active imine represented by the formula: The following three compounds can be given. Among them, the N-α-phenylethyl compound (1-
a) is more preferred.

* Represents an asymmetric carbon, and the stereochemistry of 1-a, 1-b and 1-c is RR, SR or RS
(The absolute configuration shown before the hyphen represents the absolute configuration on the 1- (trifluoromethylmonosubstituted phenyl) ethyl group side, and the absolute configuration shown after the hyphen is the chiral configuration Represents an absolute configuration on the α-arylethyl group side which is an auxiliary agent, and usually uses an R-form or S-form chiral auxiliary having 98% ee or more), and having a diastereomer excess of 10% de or more. Can be used.

[0023]

Embedded image

The inorganic acids used in the present invention include carbonic acid, hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, boric acid, perchloric acid and the like. Among them, hydrochloric acid, sulfuric acid, nitric acid and hydrobromic acid are more preferred.

The organic acids used in the present invention include acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, hexanoic acid, heptanoic acid, cyclohexanecarboxylic acid, octanoic acid, phenylacetic acid and 3-phenylpropionate. Aliphatic carboxylic acids such as acids, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, fluoroacetic acid, difluoroacetic acid,
Haloalkylcarboxylic acids such as trifluoroacetic acid, bromoacetic acid, iodoacetic acid, 2-chloropropionic acid, 3-chloropropionic acid, acrylic acid, crotonic acid, citraconic acid, maleic acid, fumaric acid, cis or trans
-Unsaturated carboxylic acids such as cinnamic acid, benzoic acid, o, m
Or p-toluic acid, o, m or p-fluorobenzoic acid, o, m or p-chlorobenzoic acid, o, m or p-bromobenzoic acid, o, m or p-iodobenzoic acid, o, m or p-hydroxybenzoic acid, o, m or p-anisic acid, o, m or p-aminobenzoic acid,
o, m or p-nitrobenzoic acid, o, m or p-cyanobenzoic acid, o, m or p-benzenedicarboxylic acid (phthalic acid, isophthalic acid, terephthalic acid), α, β or γ-picolinic acid, , 6-pyridinedicarboxylic acid,
Aromatic carboxylic acids such as 1- or 2-naphthoic acid, sulfonic acids such as methanesulfonic acid, chloromethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, p-phenolsulfonic acid, lactic acid, apple Acid, tartaric acid, dibenzoyltartaric acid, 2
-Phenylpropionic acid, mandelic acid, camphoric acid,
Optically active carboxylic acids such as cis-2-benzamidocyclohexanecarboxylic acid; phenylethanesulfonic acid;
Optically active sulfonic acids such as 0-camphorsulfonic acid,
Optically active phosphoric acids such as 2,2 ′-(1,1′-binaphthyl) phosphoric acid, optically active amino acids such as 4-aminobutyric acid, phenylglycine, aspartic acid, pyroglutamic acid, N-acetyl-3,5- Dibromo-tyrosine, N-
Optically active N-acyl amino acids such as acyl-phenylalanine, N-acyl-aspartic acid, N-acylglutamic acid, N-acylproline (N-acyl groups include acetyl, benzyloxycarbonyl, benzoyl, benzenesulfonyl Group, p-toluenesulfonyl group, etc.) and other organic acids include formic acid, oxalic acid, malonic acid, succinic acid, adipic acid, pimelic acid,
Examples include cyanoacetic acid, citric acid, glycolic acid, glyoxylic acid, pyruvic acid, levulinic acid, oxaloacetic acid, mercaptoacetic acid, phenoxyacetic acid, picric acid and the like. Optically active carboxylic acids, optically active sulfonic acids, optically active phosphoric acids, optically active amino acids or optically active N-acyl amino acids have optical isomers, and both optical isomers can be used. Among them, phthalic acid and benzenesulfonic acid are more preferable.

The amount of the acid used in the present invention is as follows:
0.1 to the optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamines represented by the general formula [1].
It is sufficient to use at least 3 molar equivalents, preferably from 0.3 to 5 molar equivalents, and more preferably from 0.3 to 3 molar equivalents.

The method for preparing the salt of the present invention comprises the steps of:
(Trifluoromethylmono-substituted phenyl) ethylamine and an acid may be appropriately determined. Usually, the optically active amine and the acid are directly added to a recrystallization solvent and mixed, or each solution is prepared in advance. It can be prepared by mixing the solutions.

The recrystallization solvent used in the present invention includes:
Optically active 1- (trifluoromethyl monosubstituted phenyl)
There is no particular limitation as long as it does not react with ethylamines, acids or salts thereof, as long as it is appropriately determined according to the diastereomeric excess before purification, or the target diastereomeric excess and recovery after purification. Good. Examples of such a recrystallization solvent include aliphatic hydrocarbons such as n-pentane, n-hexane, c-hexane and n-heptane; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene and mesitylene; methylene chloride; Chloroform,
Halogenated hydrocarbons such as 1,2-dichloroethane, ethers such as diethyl ether, tetrahydrofuran, t-butyl methyl ether, 1,4-dioxane, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, acetic acid Esters such as n-butyl, nitriles such as acetonitrile and propionitrile, methanol, ethanol, n-propanol, i-
Examples thereof include alcohols such as propanol and n-butanol, and water. Among them, n-hexane, n
-Heptane, toluene, methylene chloride, t-butyl methyl ether, acetone, ethyl acetate, acetonitrile,
Methanol, ethanol, n-propanol and i-propanol are more preferred. These solvents can be used alone or in combination.

The amount of the recrystallization solvent used in the present invention is not particularly limited as long as the salt before purification is completely or partially dissolved when heated, and the diastereomer before purification is used. It may be appropriately determined according to the excess ratio, or the target diastereomer excess ratio after purification and the recovery ratio. Usually, it is sufficient to use 1 volume or more of the salt of the optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine represented by the general formula [1], preferably 1 to 100 volumes, particularly preferably 1 to 50 volumes. Capacity is more preferred.

In the recrystallization operation of the present invention, a crystal can be deposited smoothly and efficiently by adding a seed crystal. The amount of the seed crystal used is preferably 1/10 to 1/10000 weight, more preferably 1/20 to 1/1000 weight, based on the salt before purification.

The temperature conditions for the recrystallization operation of the present invention can be appropriately determined according to the boiling point and the freezing point of the solvent used. Usually, the temperature before room temperature (25 ° C.) is about the boiling point of the recrystallization solvent, Is dissolved, and crystals can be precipitated at -40 to 80 ° C.

In the present invention, since the diastereomer excess of the precipitated crystals is improved, the precipitated crystals are recovered by filtration or the like to obtain high purity 1- (trifluoromethylmonosubstituted phenyl) ethylamines. Salt can be obtained. Further, by repeating the recrystallization operation, a product having a higher purity can be obtained. The obtained salt is used as it is or after being converted to a free base with an alkaline aqueous solution, and then subjected to hydrogenolysis to obtain the objective 1- (trifluoromethylmono-substituted phenyl) of high optical purity without racemization. ) Ethylamine can be obtained (when hydrogenolysis is carried out as a salt,
After completion of the reaction, the optically active amine can be recovered as a free base by neutralizing with an aqueous alkaline solution and extracting with an organic solvent. Further, the obtained crude product of the optically active amine can be purified, if necessary, by activated carbon, distillation, recrystallization, column chromatography or the like.

[0033]

EXAMPLES Hereinafter, the embodiments of the present invention will be described specifically with reference to Examples, but the present invention is not limited to these Examples.

The absolute configuration of the optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine shown in Reference Example was determined by comparing the sign of the measured value of the optical rotation with the sign of the literature value. Further, the absolute configuration of the synthetic intermediate was determined by carrying out hydrogenolysis and converting it into the optically active amine. % De and% ee in Examples and Reference Examples represent diastereomeric excess and enantiomeric excess, respectively, and were determined by chiral GC (CP-Chirasil-Dex CB).

Example 1 Recrystallization Purification of SS-Meta-1-a with Phthalate In 3.5 ml of i-propanol, optically active 1- (trifluoromethylmono-substituted phenyl) ethylamines (S
-S-met-1-a, diastereomer ratio / SS form:
RST (86:14) 1.00 g (3.41 mmol)
1, 1 eq) and 0.56 g of phthalic acid (3.37 mmol)
1, 1 eq) and stirred at 60-70 ° C. for 30 minutes,
5 ml of n-hexane was added, and the mixture was allowed to cool to room temperature and left for 63 hours. The precipitated crystals are filtered, washed with a small amount of n-hexane, dried in vacuo, and then crystals having the structure shown below.
36 g and 0.20 g of mother liquor were obtained. Each de is
The free base was prepared with a 0.5N NaOH aqueous solution, and chiral G
C analysis showed that 95.8% de (major body was S-S body) and 43.9% de (major body was R-S, respectively)
Body).

[0036]

Embedded image

¹ H-NMR (TMS, CDCl ₃ ):
80 (d, 7.2 Hz, 3H), 1.84 (d, 7.2
Hz, 3H), 4.01 (q, 7.2 Hz, 1H),
4.15 (q, 7.2 Hz, 1H), 7.35-7.8
8 (m, 11H), 8.48-8.59 (m, 2H),
10.60 (br, 3H).

Example 2 Recrystallization Purification of SS-Meta-1-a with Hydrobromide Optically active 1- (trifluoromethylmono-substituted phenyl) ethylamines (SS) were added to 3 ml of methanol. -Meta-1-a, diastereomer ratio / SS form: RS form =
86:14) 1.00 g (3.41 mmol, 1e)
q) and 0.4% (3.44 mmol) of 47% hydrobromic acid
1, 1 eq), stirred at 80 ° C. for 30 minutes, and concentrated under reduced pressure. The residue contains 6 ml of i-propanol and n-
6 ml of heptane was added, and the mixture was stirred at room temperature for 67 hours. The precipitated crystals were filtered, washed with a small amount of n-heptane, dried under vacuum, and 1.03 g of crystals having the structure shown below and mother liquor.
0.24 g was obtained. Each de is 0.5N-Na
The base was converted to a free base with an OH aqueous solution and subjected to chiral GC analysis.
Body), 2.9% de (major body is SS body). Further, 1.03 g of the obtained crystals was added to 10 ml of i-propanol, dissolved by heating, and 3 m of n-heptane was added.
and stirred at room temperature for 16 hours. The precipitated crystals were filtered, washed with a small amount of n-heptane, and dried under vacuum to obtain 0.78 g of crystals having the structure shown below and 0.22 g of mother liquor. Each de was converted to a free base with a 0.5N NaOH aqueous solution, and subjected to chiral GC analysis.
9.3% de (major body is SS body), 10.3% d
e (major body is SS body).

[0039]

Embedded image

¹ H-NMR (TMS, CDCl ₃ ):
00 (d, 6.8 Hz, 3H), 2.04 (d, 6.8
Hz, 3H), 3.89 (m, 1H), 4.04 (m,
1H), 7.34-8.22 (m, 9H), 10.20
(Br, 2H).

Example 3 Recrystallization Purification of SS-Para-1-a with Phthalate In 3.5 ml of i-propanol, optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamines (S
-S-para-1-a, diastereomer ratio / SS form:
RST (84:16) 1.00 g (3.41 mmol)
1, 1 eq) and 0.56 g of phthalic acid (3.37 mmol)
1, 1 eq) and stirred at 60-70 ° C. for 30 minutes,
5 ml of n-hexane was added, and the mixture was allowed to cool to room temperature and left for 23 hours. The precipitated crystals are filtered, washed with a small amount of n-hexane, dried in vacuo, and then crystals having the structure shown below.
24 g and 0.30 g of mother liquor were obtained. Each de is
The free base was prepared with a 0.5N NaOH aqueous solution, and chiral G
C analysis revealed that each was 93.8% de (major body was S-S body) and 51.5% de (major body was R-S body).
Body). Further, 1.20 g of the obtained crystal was
-Propanol (3 ml), the mixture was stirred at 60 to 70 ° C for 30 minutes, n-hexane (2 ml) was added, and the mixture was allowed to cool to room temperature and left for 2 hours. The precipitated crystals are filtered and a small amount of n
After washing with -hexane and vacuum drying, 1.08 g of crystals having the structure shown below and 0.12 g of mother liquor were obtained. Each d
e was made into a free base with a 0.5N NaOH aqueous solution and subjected to chiral GC analysis. As a result, 99.0% de (major form was SS form) and 26.1% de (major form was SS form), respectively. )Met.

[0042]

Embedded image

¹ H-NMR (TMS, CDCl ₃ ):
80 (d, 6.8 Hz, 6H), 4.04 (q, 6.8
Hz, 1H), 4.13 (q, 6.8 Hz, 1H),
7.35-7.73 (m, 11H), 8.45-8.5
5 (m, 2H), 10.60 (br, 3H).

Example 4 Recrystallization Purification of SS-Para-1-a with Benzene Sulfonate In 3.5 ml of i-propanol, optically active 1- (trifluoromethylmono-substituted phenyl) ethylamines ( S
-S-para-1-a, diastereomer ratio / SS form:
RST (84:16) 1.00 g (3.41 mmol)
1, 1 eq) and benzenesulfonic acid monohydrate 0.6
0 g (3.41 mmol, 1 eq), and
After stirring at 30 ° C. for 30 minutes, 5 ml of n-hexane was added, and the mixture was allowed to cool to room temperature and left for 1 day. The precipitated crystals were collected by filtration, washed with a small amount of n-hexane, and dried under vacuum to obtain 1.32 g of crystals having the structure shown below and 0.20 g of mother liquor.
Each de was converted to a free base with a 0.5N-NaOH aqueous solution and subjected to chiral GC analysis.
9% de (major body is SS body), 11.7% de
(The major body was an RS body). Further, 1.32 g of the obtained crystal was added to 3.9 ml of i-propanol, and the mixture was stirred at 60 to 70 ° C. for 30 minutes, and then mixed with 2 m of n-hexane.
The mixture was allowed to cool to room temperature and left overnight. The precipitated crystals were collected by filtration, washed with a small amount of n-hexane, and dried in vacuo.
g was obtained. Each de was converted to a free base with a 0.5N-NaOH aqueous solution and subjected to chiral GC analysis. As a result, 98.6% de (major form is SS form) and 17.
It was 6% de (the major body was an RS body).

[0045]

Embedded image

¹ H-NMR (TMS, CDCl ₃ ):
84 (d, 5.6 Hz, 6H), 3.84 (q, 5.6
Hz, 1H), 3.95 (q, 5.6 Hz, 1H),
7.20-7.60 (m, 12H), 8.03-8.1
7 (m, 2H), 9.73 (br, 2H).

Reference Example 1 / Purified SS-Meta-1
Conversion of -a-phthalate to optically active 1- (meta-trifluoromethylphenyl) ethylamine To 10 ml of toluene was added SS-met-1-a-phthalate purified in Example 1 (95.8). % De) 1.00
g (2.18 mmol, 1 eq) and 0.5 N NaOH
An aqueous solution (17.4 ml, 8.72 mmol, 4 eq) was added, and the mixture was stirred at room temperature for 30 minutes. After static separation, the recovered aqueous layer was extracted with 5 ml of toluene, and the combined recovered organic layer was washed with saturated saline. Dried over anhydrous sodium sulfate, filtered,
After concentration and vacuum drying, the SS-meta-1 having the structure shown in the following formula
-A was obtained in quantitative yield.

[0048]

Embedded image

The obtained SS-meta-1-a was dissolved in 2.2 ml of methanol, and 5% palladium / activated carbon (5%) was added.
12.8 mg (2% by weight) was added, the hydrogen pressure was set to 0.5 MPa, and the mixture was stirred at 60 ° C for 24 hours. The reaction-terminated liquid was filtered through celite, concentrated, dried in vacuo,
A crude product of (S) -1- (meta-trifluoromethylphenyl) ethylamine having the structure shown below was obtained. The conversion and optical purity of the crude product were determined by chiral GC analysis and were 96% and 95.6% ee, respectively.

[0050]

Embedded image

Reference Example 2 / Purified SS-Para-1
Conversion of -a-phthalate to optically active 1- (para-trifluoromethylphenyl) ethylamine To 10 ml of toluene was added SS-para-1-a-phthalate purified in Example 3 (99.0). % De) 1.00
g (2.18 mmol, 1 eq) and 0.5 N NaOH
An aqueous solution (17.4 ml, 8.72 mmol, 4 eq) was added, and the mixture was stirred at room temperature for 30 minutes. After static separation, the recovered aqueous layer was extracted with 5 ml of toluene, and the combined recovered organic layer was washed with saturated saline. Dried over anhydrous sodium sulfate, filtered,
After concentration and vacuum drying, the SS-para-1 having the structure shown by the following formula:
-A was obtained in quantitative yield.

[0052]

Embedded image

The obtained SS-para-1-a was dissolved in 2.2 ml of methanol, and 5% palladium / activated carbon (5%) was added.
12.8 mg (2% by weight) was added, the hydrogen pressure was set to 0.5 MPa, and the mixture was stirred at 60 ° C for 24 hours. The reaction-terminated liquid was filtered through celite, concentrated, dried in vacuo,
A crude product of (S) -1- (para-trifluoromethylphenyl) ethylamine having the structure shown below was obtained. The conversion and optical purity of the crude product were determined by chiral GC analysis and were 97% and 98.9% ee, respectively.

[0054]

Embedded image

Reference Example 3 / Purified SS-para-1
Conversion of -a-benzenesulfonate to optically active 1- (para-trifluoromethylphenyl) ethylamine In 10 ml of toluene, the SS-para-1-a-benzenesulfonate purified in Example 4 (98 .6% de)
1.00 g (2.22 mmol, 1 eq) and 0.5N
-NaOH aqueous solution 13.3 ml (6.66 mmol,
3eq), and the mixture was stirred at room temperature for 30 minutes.
The recovered aqueous layer was extracted with 5 ml of toluene, and the combined recovered organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered, concentrated, and vacuum-dried.
-Para-1-a was obtained in quantitative yield.

[0056]

Embedded image

The obtained SS-para-1-a was dissolved in 2.2 ml of methanol, and 5% palladium / activated carbon (5%) was added.
13.0 mg (2% by weight) was added, the hydrogen pressure was set to 0.5 MPa, and the mixture was stirred at 60 ° C for 24 hours. The reaction-terminated liquid was filtered through celite, concentrated, dried in vacuo,
A crude product of (S) -1- (para-trifluoromethylphenyl) ethylamine having the structure shown below was obtained. The conversion and optical purity of the crude product were determined by chiral GC analysis and were 97% and 98.4% ee, respectively.

[0058]

Embedded image

[0059]

The optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine, which is an important intermediate of pharmaceuticals and agricultural chemicals, can be industrially simply and efficiently purified to a high optical purity.

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Katsu Kuriyama 2805 Imafukunakadai, Kawagoe-shi, Saitama Central Chemical Glass Co., Ltd. (72) Inventor Masatomi Kanai 2805 Imafukunakadai, Kawagoe-shi, Saitama Central Glass Inside the Chemical Research Laboratory Co., Ltd. (72) Inventor Takashi Hayami 2805 Imafukunakadai, Kawagoe-shi, Saitama Central Glass Inside the Chemical Research Laboratories F-term (reference) 4H006 AA01 AA02 AB84 AC83 AD15 AD33

Claims (8)

[Claims] 1. A compound of the general formula [1] [Wherein, R represents an optically active α- represented by C * HMeAr.
Represents an arylethyl group, and Ar is a phenyl group or 1
Or represents a 2-naphthyl group, and * represents an asymmetric carbon]. The optically active 1- (trifluoromethylmono-substituted phenyl) ethylamine represented by the formula: Characteristic purification method. 2. The method according to claim 1, wherein the inorganic acid is selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, and hydrobromic acid. 3. The method according to claim 1, wherein the organic acid is selected from the group consisting of benzenesulfonic acid and phthalic acid. 4. The purification method according to claim 1, wherein the stereochemistry of * in the general formula [1] is R-form or S-form. 5. A compound of the general formula [1] [Wherein, R represents an optically active α- represented by C * HMeAr.
Represents an arylethyl group, and Ar is a phenyl group or 1
Or, * represents a 2-naphthyl group, and * represents an asymmetric carbon.] An inorganic or organic acid salt of an optically active 1- (trifluoromethylmonosubstituted phenyl) ethylamine represented by the formula: 6. The salt according to claim 5, wherein the inorganic acid is selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid and hydrobromic acid. 7. The salt according to claim 5, wherein the organic acid is selected from the group consisting of benzenesulfonic acid and phthalic acid. 8. The salt according to claim 5, wherein the stereochemistry of * in the general formula [1] is R-form or S-form.